My Next 100 Days

An Experiment In Developing Focus And Consistency

I’ve always been the type who’s interested in a ton of different things. Being curious is definitely a strong suit of mine and for the most part it’s great. I constantly feel the need to figure everything out and as a result, I’m always learning. But I also think it’s important to examine where our strong suits inhibit us. Every strength comes with an unintended weakness, and for me being curious has always been served with a large glass of scatterbrain. I have a tendency to get fired up about a topic or hobby, learn enough about it to get by and move on. It’s as though one thing can’t hold my attention long enough to prevent another from stealing me away.

Taking a step back for a second, I feel great about what I’ve accomplished so far. Knowing a little bit about a lot has been really advantageous in my career. (My self appointed title bounces between “expert generalist” and “student of the world”.) And yes, there are areas in technology and finance that I’d say I’m an expert (or close to an expert) in. But what I’ve done isn’t the point here. The point is what I strive to do, and imagine I’ll accomplish a lot more in my next 32 years with more focus.

I often get worried that I’ll become“good enough” at a variety of things and never really great at anything.

So this year, I’m changing my approach based on two separate revelations:

Examining My Consistent Complaints.

One of my favorite new ways to tackle self improvement is by examining my “consistent complaints”, or the roadblocks I seem to run into over and over again in various aspects of my life. If you can figure out what your consistent complaints are, you can more easily determine what’s really stopping you and work to break through. And what I’ve learned from this exercise is that the problem never really lies within the complaint itself. Nor does it lie within any one specific issue, situation, or person. For me, the solution is always 100% of the time either an action I need to take that I’m not, or an action I need to stop. Therefore the problem doesn’t lie within the complaint, but within the reason I’m taking or not taking action.

Revelation #1 —
The problem never really lies within the complaint itself. The problem lies within the reason I’m not taking action, and the solution is always the action itself.


For years I complained about not having enough time. With all my interests in mind, I was worried about “fitting it all in” and accomplishing everything I wanted to accomplish within my lifetime.

Let’s for a second investigate just how just absolutely crazy it is to complain about time. First off, every single person on the planet has the exact same amount of time in each day. Fact. Second, we are all in complete control over how we spend our time. Even if at times it doesn’t feel so, it is. You’re in control. No one forced you to get that job, buy that puppy, live in that apartment in that city, spend time with that person, and so on. (There are of course extreme exceptions to this, but for the most part it’s true. Especially if you’re lucky enough to reside here in the US.)

So now that we know how completely insane complaining about time is, where did my issue really lie? What was I actually complaining about? What actions needed to be changed or taken?

About a year ago, I was having dinner with my good friend Jen. Jen mentioned a favorite magazine of hers called The Great Discontent and a friend of hers who was writing handwritten letters for 100 days in a row. Aptly named #The100DayProject, the idea is to tackle a project by consistently doing a thing (making, performing, writing, trying, acting, playing, etc.) for 100 days straight. The goal isn’t on finalized products, but rather the process and showing up every day. To forget about outcomes and become immersed in the process of creating. I was intrigued.

I now know the 100 day concept to be fairly common in creative industries, but at the time (and coming from Finance only a year earlier) I had never thought about attacking my career interests or outside hobbies in “sprints” before. And letting go in the process of creating? Definitely not my thing.

Fast forward a year and it seems so simple in retrospect. The solution to my consistent complaint about time wasn’t about time at all. I didn’t need to “fit it all in”. In fact I had to do the exact opposite.

Revelation #2 —
The goal isn’t on finalized products, but rather the process and showing up every day. To forget about outcomes and become immersed in the process of creating.

Focus And Plan.

I realized that when it came to my anxiety about focus, I had only been exploring and analyzing my interests. I hadn’t been planning and acting. I realized that I could accomplish it all if I had a plan.

At the beginning of each year since 2011 I’ve made a list. The list consists of 10 things that will define personal success in the coming year. As we begin 2017, I’m approaching the list a little differently.

First, I’m getting focused. Earlier this year I made a list of things I do on a weekly basis, from work to hobbies, and then another of things I want to try or do more of. I categorized the lists between work and outside work. I tried to keep the list big picture. (I like lists.)

Here it is from my iPhone notes.

Things I do now:


  • Building team and culture at Jakt
  • Handling all thing operations and finance at Jakt
  • Consulting Jakt partners
  • Business development for Jakt
  • Investing in companies (sparingly)
  • Building community and connecting people
  • Hosting and attending events in related industries

Outside Work

  • Exercise — SoulCycle, boxing, yoga, strength training
  • Traveling or planning my next trip
  • My “No Agenda” dinner series
  • Snowboarding
  • Live music events
  • Socializing and seeing my friends
  • Netflix and chilling out

Things I want to try or do more of:


  • Speaking engagements, sitting on panels
  • Ideating on and building my own products
  • Advising companies or becoming a board member
  • Additional writing and thought leadership pieces
  • Podcasting or vlogging

Outside Work

  • Reading more fiction
  • Playing soccer
  • Improving my golf game
  • Taking more photos with my camera
  • Learning to produce music
  • Becoming fluent in Spanish
  • Becoming a better guitar player

Second, I’m applying the 100 day logic to three projects that are outside the norm of my routine. Since my company Jakt is my top career priority at the moment, the list below is unrelated to my career. (Jakt has its own set of priorities and goals which Anthony and I plan to publicize separately).

100 Day Sprints

  1. Speak Spanish for 10 minutes everyday for 100 days in a row
  2. Play guitar for 10 minutes everyday for 100 days in a row
  3. Read fiction for 10 minutes everyday for 100 days in a row.

Lastly, I’m making my yearly list public to hold myself accountable. In addition to this blog post, I created a separate section on my website ( where you can follow along with my progress. Hopefully it will inspire someone to sprint on a few new projects this year.

10 Things that will define personal success in 2017

  1. Travel to 3 new places
  2. Meditate for at least 10 minutes every day
  3. Exercise at least 6x per week every week
  4. Produce 24 blog posts (2x per month)
  5. Grow my online following 5x
  6. Journal 1x per day, every day
  7. Cut sugar consumption 50%
  8. Attend 1 event outside startups/tech (art, music, fashion, etc.) per month
  9. Play 5 rounds of golf
  10. Snowboard 3 times


In mid-2016 I visited Nicaragua. Even with years of Spanish class under my belt I spoke English to all of the locals, embarrassed that my lingo wasn’t good enough. For no other reason than sheer embarrassment, I’ve decided to start with Spanish and I’ve been speaking Spanish for 5 minutes a day for the past 3 weeks. Yesterday I upped that 5 minutes to 10 and according to Duolingo I’m about 5% fluent in Spanish. My hope is to get to 50% over the next 100 days and take it from there.

Every strength may come with an unintended weakness, but that’s totally okay. It doesn’t have to end there. I believe that by taking action, I can challenge my consistent complaints. See you in 100 days.

Happy New Year.